SILDENAFIL

Details

Stereochemistry	ACHIRAL
Molecular Formula	C22H30N6O4S
Molecular Weight	474.576
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCC1=NN(C)C2=C1N=C(NC2=O)C3=CC(=CC=C3OCC)S(=O)(=O)N4CCN(C)CC4

InChI

InChIKey=BNRNXUUZRGQAQC-UHFFFAOYSA-N

InChI=1S/C22H30N6O4S/c1-5-7-17-19-20(27(4)25-17)22(29)24-21(23-19)16-14-15(8-9-18(16)32-6-2)33(30,31)28-12-10-26(3)11-13-28/h8-9,14H,5-7,10-13H2,1-4H3,(H,23,24,29)

HIDE SMILES / InChI

Molecular Formula	C22H30N6O4S
Molecular Weight	474.576
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020895s045lbl.pdf | http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/021845s016,022473s010,203109s009lbl.pdf

Sildenafil (Viagra, Revatio) is a PDE5 inhibitor which was approved by FDA for the treatment of erectile disfunction and adults with pulmonary arterial hypertension. Upon administration sildenafil inhibits PDE5 and results in elevated level of cyclic guanosine monophosphate and smooth muscle relaxation.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Phosphodiesterase 5A 31 Target ID: CHEMBL1827 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020895s045lbl.pdf	Inhibitor 8504		3.5 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Erectile dysfunction 35 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020895s045lbl.pdf	Curative		Approved 8583	VIAGRA Approved Use VIAGRA is a phosphodiesterase-5 (PDE5) inhibitor indicated for the treatment of erectile dysfunction. Launch Date 1998
Pulmonary arterial hypertension 36 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/021845s016,022473s010,203109s009lbl.pdf	Primary		Approved 8583	REVATIO Approved Use REVATIO is a phosphodiesterase-5 (PDE-5) inhibitor indicated for the treatment of pulmonary arterial hypertension (PAH) (WHO Group I) in adults to improve exercise ability and delay clinical worsening. Launch Date 2005

C_max

Value	Dose	Co-administered	Analyte	Population
159 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/11879254	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:		SILDENAFIL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
530 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/11879254	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:		SILDENAFIL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
4 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/20895s039s042lbl.pdf	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:		SILDENAFIL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
4.07 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/11879254	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:		SILDENAFIL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

F_unbound

Value	Dose	Co-administered	Analyte	Population
4% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/20895s039s042lbl.pdf	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:		SILDENAFIL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
2000 mg single, oral Overdose Dose: 2000 mg Route: oral Route: single Dose: 2000 mg Sources: https://pubmed.ncbi.nlm.nih.gov/26139313	healthy, 33 Health Status: healthy Age Group: 33 Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/26139313	Disc. AE: Flushing, Headache... AEs leading to discontinuation/dose reduction: Flushing Headache Tachycardia (mild) Sources: https://pubmed.ncbi.nlm.nih.gov/26139313
2400 mg single, oral Overdose Dose: 2400 mg Route: oral Route: single Dose: 2400 mg Sources: https://pubmed.ncbi.nlm.nih.gov/26139313	healthy, 33 Health Status: healthy Age Group: 33 Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/26139313	Disc. AE: Visual field defect... AEs leading to discontinuation/dose reduction: Visual field defect Sources: https://pubmed.ncbi.nlm.nih.gov/26139313
250 mg single, oral Overdose Dose: 250 mg Route: oral Route: single Dose: 250 mg Sources: https://pubmed.ncbi.nlm.nih.gov/24661860	unhealthy, 45 Health Status: unhealthy Age Group: 45 Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/24661860	Disc. AE: Rhabdomyolysis, Visual disturbance NOS... AEs leading to discontinuation/dose reduction: Rhabdomyolysis Visual disturbance NOS Sources: https://pubmed.ncbi.nlm.nih.gov/24661860
80 mg 3 times / day multiple, oral Highest studied dose Dose: 80 mg, 3 times / day Route: oral Route: multiple Dose: 80 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/21546436	unhealthy, 47.5 Health Status: unhealthy Age Group: 47.5 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/21546436	Sources: https://pubmed.ncbi.nlm.nih.gov/21546436
6.5 g single, oral Overdose Dose: 6.5 g Route: oral Route: single Dose: 6.5 g Sources: https://pubmed.ncbi.nlm.nih.gov/26139313	healthy, 56 Health Status: healthy Age Group: 56 Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/26139313	Disc. AE: Vomiting, Blurred vision... AEs leading to discontinuation/dose reduction: Vomiting (severe) Blurred vision Sinus tachycardia Sources: https://pubmed.ncbi.nlm.nih.gov/26139313
600 mg single, oral Overdose Dose: 600 mg Route: oral Route: single Dose: 600 mg Sources: https://pubmed.ncbi.nlm.nih.gov/26139313 https://pubmed.ncbi.nlm.nih.gov/12507258	healthy, 56 Health Status: healthy Age Group: 56 Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/26139313 https://pubmed.ncbi.nlm.nih.gov/12507258	Disc. AE: Cardiomegaly, Fibrosis myocardial... AEs leading to discontinuation/dose reduction: Cardiomegaly (grade 5) Fibrosis myocardial (grade 5) Sources: https://pubmed.ncbi.nlm.nih.gov/26139313 https://pubmed.ncbi.nlm.nih.gov/12507258
100 mg 1 times / day multiple, oral Recommended Dose: 100 mg, 1 times / day Route: oral Route: multiple Dose: 100 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/9580646	unhealthy, 58 Health Status: unhealthy Age Group: 58 Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/9580646	Disc. AE: Nausea, Vomiting... AEs leading to discontinuation/dose reduction: Nausea (0.32%) Vomiting (0.32%) Leg pain (0.32%) Backache (0.32%) Intermittent headache (0.32%) Dyspepsia (0.32%) Headache (0.32%) Sources: https://pubmed.ncbi.nlm.nih.gov/9580646
100 mg 1 times / day multiple, oral Recommended Dose: 100 mg, 1 times / day Route: oral Route: multiple Dose: 100 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/9580646	unhealthy, 60 Health Status: unhealthy Age Group: 60 Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/9580646	Disc. AE: Headache, Flushing... AEs leading to discontinuation/dose reduction: Headache (0.61%) Flushing (0.61%) Sources: https://pubmed.ncbi.nlm.nih.gov/9580646
100 mg 1 times / day multiple, oral Recommended Dose: 100 mg, 1 times / day Route: oral Route: multiple Dose: 100 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/9580646	unhealthy, 60 Health Status: unhealthy Age Group: 60 Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/9580646	Disc. AE: Headache, Flushing... AEs leading to discontinuation/dose reduction: Headache (0.9%) Flushing (0.44%) Blurred vision (0.44%) Groin pain (1.3%) Sources: https://pubmed.ncbi.nlm.nih.gov/9580646
400 mg single, oral Overdose Dose: 400 mg Route: oral Route: single Dose: 400 mg Sources: https://pubmed.ncbi.nlm.nih.gov/30473955	unhealthy, 67 Health Status: unhealthy Age Group: 67 Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/30473955	Disc. AE: Acute kidney injury... AEs leading to discontinuation/dose reduction: Acute kidney injury Sources: https://pubmed.ncbi.nlm.nih.gov/30473955

AEs

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:9139	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:9139
ChemicalBook	CB2747316	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB2747316
ChemicalBook	CB82675677	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB82675677
eMolecules	902463	https://www.emolecules.com/cgi-bin/more?vid=902463
MolPort	MolPort-001-995-394	https://www.molport.com/shop/molecule-link/MolPort-001-995-394
MolPort	MolPort-002-885-861	https://www.molport.com/shop/molecule-link/MolPort-002-885-861
MolPort	MolPort-046-854-547	https://www.molport.com/shop/molecule-link/MolPort-046-854-547
MolPort	MolPort-047-113-940	https://www.molport.com/shop/molecule-link/MolPort-047-113-940
ZINC	ZINC000019796168	http://zinc15.docking.org/substances/ZINC000019796168

PubMed

Title	Date	PubMed
Subjective visual halos after sildenafil (Viagra) administration: Electroretinographic evaluation.	2001-05	11320016
Antimitogenic actions of organic nitrates are potentiated by sildenafil and mediated via activation of protein kinase A.	2001-05	11306686
FIA of sildenafil citrate using UV-detection.	2001-05	11275442
Studies of Viagra offer some reassurance to men with concerns about cardiac effects.	2001-04-18	11308415
Safe use of sildenafil in patients with coronary artery disease.	2001-04	11326814
Cost-sharing for prescriptions of sildenafil and finasteride: a case study in veteran patients.	2001-04	11310190
Sildenafil citrate effectively reverses sexual dysfunction induced by three-dimensional conformal radiation therapy.	2001-04	11306401
Sildenafil citrate for penile hemodynamic determination: an alternative to intracavernosal agents in Doppler ultrasound evaluation of erectile dysfunction.	2001-04	11306361
Modulation of human platelet aggregation by the phosphodiesterase type 5 inhibitor sildenafil.	2001-04	11300654
Efficacy and safety of sildenafil citrate in the treatment of men with mild to moderate erectile dysfunction.	2001-04	11282811
Intracavernosal injection of sildenafil citrate: misapplication of the drug.	2001-04	11257683
[Side effects of sildenafil: findings from two years practical experience].	2001-03-17	11284286
Cardiovascular events in users of sildenafil: results from first phase of prescription event monitoring in England.	2001-03-17	11250850
Narrowbore high-performance liquid chromatography for the simultaneous determination of sildenafil and its metabolite UK-103,320 in human plasma using column switching.	2001-03-05	11254188
Viagra: a three-year sexual revolution and the need to recognise its role within the NHS.	2001-03	11321862
Three-year update of sildenafil citrate (Viagra) efficacy and safety.	2001-03	11321851
Initial uptake in use of sildenafil in general practice.	2001-03	11317480
Anterior ischemic optic neuropathy associated with viagra.	2001-03	11315976
Identification of the cytochrome P450 enzymes involved in the N-demethylation of sildenafil.	2001-03	11298070
Alternatives to Viagra.	2001-03	11286776
Is brachytherapy comparable with radical prostatectomy and external-beam radiation for clinically localized prostate cancer?	2001-03	11272667
Sildenafil citrate and sperm function.	2001-03	11262489
Is the sildenafil product information adequate to facilitate informed therapeutic decisions?	2001-03	11261532
Comparison of FDA reports of patient deaths associated with sildenafil and with injectable alprostadil.	2001-03	11261524
Combination of phentolamine and L-arginine or sildenafil synergistically improves neurogenic relaxation of rabbit corpus cavernosum smooth muscle.	2001-03	11248652
Relapse prevention strategies and techniques with erectile dysfunction.	2001-02-28	11224950
[Research on impotence and marketing].	2001-02-20	11301624
[Endocrinology 1999-2000].	2001-02-15	11284421
Sildenafil-simvastatin interaction: possible cause of rhabdomyolysis?	2001-02-15	11237079
Assessment of as needed use of pharmacotherapy and the pause-squeeze technique in premature ejaculation.	2001-02	11313839
Oral alpha adrenoceptor blockade as a treatment of erectile dysfunction.	2001-02	11289574
Central effects of sildenafil (Viagra) on auditory selective attention and verbal recognition memory in humans: a study with event-related brain potentials.	2001-02	11289570
Sildenafil citrate, a selective phosphodiesterase type 5 inhibitor: urologic and cardiovascular implications.	2001-02	11289569
Changes in ED therapy in the Viagra era.	2001-02	11289566
Phosphodiesterase isoenzymes as pharmacological targets in the treatment of male erectile dysfunction.	2001-02	11289565
Intracerebral haemorrhage associated with sildenafil citrate.	2001-02	11284133
I've heard of an herbal alternative to Viagra for impotence. Does it work and is it safe?	2001-02	11216037
Efficacy of oral sildenafil in the treatment of erectile dysfunction in diabetic men with positive response to intracavernosal injection of alprostadil.	2001-02	11213904
Sildenafil citrate (VIAGRA) improves erectile function in elderly patients with erectile dysfunction: a subgroup analysis.	2001-02	11213274
[Drug treatment of erection disorders in patients with cardiovascular disease].	2001-01-27	11213561
[Erectile dysfunction in coronary heart disease. No fear about the blue pill].	2001-01-18	11215348
[Paths to sexual satisfaction. What will stimulate the tired man?].	2001-01-18	11215339
[Prescribing of sildenafil by national insurance program physicians. What basic sexual medicine qualification is required?].	2001-01-11	11217683
The role of nitric oxide in penile erection.	2001-01	11336572
Emergency sperm extraction for transient erectile dysfunction prior to assisted conception.	2001-01	11292994
Sildenafil citrate: a therapeutic update.	2001-01	11219477
A risk-benefit assessment of sildenafil in the treatment of erectile dysfunction.	2001	11330655
Use of sildenafil in penile implant patients.	2001	11316977
'Viagra effect' - influence of mass media on patient behavior.	2001	11316976
Strategies for the treatment of antidepressant-related sexual dysfunction.	2001	11229451

Patents

Sample Use Guides

In Vivo Use Guide

Erectile disfunction: For most patients, the recommended dose is 50 mg taken, as needed, approximately 1 hour before sexual activity. Pulmonary arterial hypertension: 5 mg or 20 mg three times a day, 46 hours apart (oral); 2.5 mg or 10 mg three times a day administered as an intravenous bolus injection.

Route of Administration: Other

In Vitro Use Guide

Human bladder samples were treated with sildenafil (10 nM–30 µM) to test the ability of the drug to inhibit contraction.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:05:09 GMT 2025` Edited by `admin` on `Mon Mar 31 18:05:09 GMT 2025`
Record UNII	3M7OB98Y7H
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

APHRODIL

Preferred Name

English

SILDENAFIL

Official Name

English

SILDENAFIL [VANDF]

Common Name

English

SILDENAFIL RATIOPHARM

Brand Name

English

HIP-0908

Code

English

VIZARSIN

Brand Name

English

PIPERAZINE, 1-((3-(6,7-DIHYDRO-1-METHYL-7-OXO-3-PROPYL-1H-PYRAZOLO(4,3-D)PYRIMIDIN-5-YL)-4-ETHOXYPHENYL)SULFONYL)-4-METHYL-

Systematic Name

English

SILDENAFIL [MI]

Common Name

English

Sildenafil [WHO-DD]

Common Name

English

HIP0908

Code

English

SILDENAFIL [EMA EPAR]

Common Name

English

SILDENAFIL ACTAVIS

Brand Name

English

1-((3-(6,7-DIHYDRO-1-METHYL-7-OXO-3-PROPYL-1H-PYRAZOLO(4,3-D)PYRIMIDIN-5-YL)-4-ETHOXYPHENYL)SULFONYL)-4-METHYLPIPERAZINE

Systematic Name

English

SILDENAFIL [HSDB]

Common Name

English

SILDENAFIL TEVA

Brand Name

English

PATREX

Brand Name

English

sildenafil [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C2127